Brodimoprim-4,6-Dicarboxylate

Identification

Name
Brodimoprim-4,6-Dicarboxylate
Accession Number
DB02809  (EXPT00651)
Type
Small Molecule
Groups
Experimental
Description

Brodimoprim-4,6-dicarboxylate is a solid. This compound belongs to the anisoles. These are organic compounds contaiing a methoxybenzene or a derivative thereof. This medication is known to target the protein dihydrofolate reductase.

Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 496.332
Monoisotopic: 495.087922167
Chemical Formula
C20H24BrN4O6
InChI Key
SZAVCZNFKJSWRN-LBPRGKRZSA-M
InChI
InChI=1S/C20H25BrN4O6/c1-30-14-8-11(7-13-10-24-20(23)25-18(13)22)9-15(17(14)21)31-6-2-3-12(19(28)29)4-5-16(26)27/h8-10,12H,2-7H2,1H3,(H,26,27)(H,28,29)(H4,22,23,24,25)/p-1/t12-/m0/s1
IUPAC Name
2,4-diamino-5-[(4-bromo-3-{[(4S)-4,6-dicarboxylatohexyl]oxy}-5-methoxyphenyl)methyl]pyrimidin-1-ium
SMILES
COC1=CC(CC2=C[NH+]=C(N)N=C2N)=CC(OCCC[C@@H](CCC([O-])=O)C([O-])=O)=C1Br

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDihydrofolate reductaseNot AvailableLactobacillus casei
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
5287754
PubChem Substance
46507558
ChemSpider
4450057
HET
BDM
PDB Entries
1dis / 1diu

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00803 mg/mLALOGPS
logP0.94ALOGPS
logP0.82ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)3.05ChemAxon
pKa (Strongest Basic)7.16ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area177.79 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity140.09 m3·mol-1ChemAxon
Polarizability45.66 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6298
Blood Brain Barrier+0.7277
Caco-2 permeable-0.5596
P-glycoprotein substrateSubstrate0.5253
P-glycoprotein inhibitor INon-inhibitor0.9207
P-glycoprotein inhibitor IINon-inhibitor0.9114
Renal organic cation transporterNon-inhibitor0.7495
CYP450 2C9 substrateNon-substrate0.8765
CYP450 2D6 substrateNon-substrate0.842
CYP450 3A4 substrateNon-substrate0.5954
CYP450 1A2 substrateNon-inhibitor0.5894
CYP450 2C9 inhibitorNon-inhibitor0.7227
CYP450 2D6 inhibitorNon-inhibitor0.8249
CYP450 2C19 inhibitorNon-inhibitor0.5694
CYP450 3A4 inhibitorNon-inhibitor0.8676
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7291
Ames testNon AMES toxic0.6723
CarcinogenicityNon-carcinogens0.9568
BiodegradationNot ready biodegradable0.9143
Rat acute toxicity2.3534 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8204
hERG inhibition (predictor II)Non-inhibitor0.8022
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol ethers
Sub Class
Anisoles
Direct Parent
Anisoles
Alternative Parents
Phenoxy compounds / Methoxybenzenes / Medium-chain fatty acids / Alkyl aryl ethers / Aminopyrimidines and derivatives / Branched fatty acids / Bromobenzenes / Halogenated fatty acids / Heterocyclic fatty acids / Aryl bromides
show 15 more
Substituents
Phenoxy compound / Anisole / Methoxybenzene / Medium-chain fatty acid / Alkyl aryl ether / Aminopyrimidine / Branched fatty acid / Bromobenzene / Halobenzene / Halogenated fatty acid
show 33 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
organobromine compound, aminopyrimidine (CHEBI:47236)

Targets

Kind
Protein
Organism
Lactobacillus casei
Pharmacological action
Unknown
General Function
Nadp binding
Specific Function
Key enzyme in folate metabolism. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis.
Gene Name
folA
Uniprot ID
P00381
Uniprot Name
Dihydrofolate reductase
Molecular Weight
18438.73 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:23